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MedKoo Cat#: 531002 | Name: Antipyrine
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Antipyrine, also known as Phenazone, is an analgesic and anti-inflammatory. Antipyrine (AP) metabolism was used to assess factors associated with the activity of hepatic oxidative enzymes in firefighters. The antipyrine test can be used as metabolic probe of biological response to recent dioxin exposure.

Chemical Structure

Antipyrine
Antipyrine
CAS#60-80-0

Theoretical Analysis

MedKoo Cat#: 531002

Name: Antipyrine

CAS#: 60-80-0

Chemical Formula: C11H12N2O

Exact Mass: 188.0950

Molecular Weight: 188.23

Elemental Analysis: C, 70.19; H, 6.43; N, 14.88; O, 8.50

Price and Availability

Size Price Availability Quantity
5g USD 150.00 Ready to ship
25g USD 250.00 Ready to ship
50g USD 350.00 2 Weeks
100g USD 550.00 2 weeks
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Related CAS #
No Data
Synonym
Antipyrine, Phenazone, Azophen, NSC 7945, NSC 7945, NSC 7945, Auralgan
IUPAC/Chemical Name
1,5-dimethyl-2-phenyl-1,2-dihydro-3H-pyrazol-3-one
InChi Key
VEQOALNAAJBPNY-UHFFFAOYSA-N
InChi Code
InChI=1S/C11H12N2O/c1-9-8-11(14)13(12(9)2)10-6-4-3-5-7-10/h3-8H,1-2H3
SMILES Code
O=C1N(C2=CC=CC=C2)N(C)C(C)=C1
Appearance
White to light yellow crystalline powder.
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 188.23 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Chernyak YI, Merinova AP, Shelepchikov AA, Kolesnikov SI, Grassman JA. Impact of dioxins on antipyrine metabolism in firefighters. Toxicol Lett. 2016 May 27;250-251:35-41. doi: 10.1016/j.toxlet.2016.04.006. Epub 2016 Apr 8. PubMed PMID: 27067104. 2: Zhang R, Song R, Sun Y, Hao Q. Synthesis, structure and photoresponsive properties of 4-(3-fluorobenzylideneamino)antipyrine. Spectrochim Acta A Mol Biomol Spectrosc. 2013 Sep;113:43-51. doi: 10.1016/j.saa.2013.04.099. Epub 2013 May 7. PubMed PMID: 23711396. 3: Abualhasan MN, Batrawi N, Zaid AN, Watson DG. A validated and stability indicating HPLC method for analysis of diminazene aceturate and antipyrine combination in a ready injectable solution. Drug Res (Stuttg). 2013 Jun;63(6):300-4. doi: 10.1055/s-0033-1337939. Epub 2013 Mar 26. PubMed PMID: 23532624. 4: Jiao SS, Yao XQ, Liu YH, Wang QH, Zeng F, Lu JJ, Liu J, Zhu C, Shen LL, Liu CH, Wang YR, Zeng GH, Parikh A, Chen J, Liang CR, Xiang Y, Bu XL, Deng J, Li J, Xu J, Zeng YQ, Xu X, Xu HW, Zhong JH, Zhou HD, Zhou XF, Wang YJ. Edaravone alleviates Alzheimer's disease-type pathologies and cognitive deficits. Proc Natl Acad Sci U S A. 2015 Apr 21;112(16):5225-30. doi: 10.1073/pnas.1422998112. Epub 2015 Apr 6. PubMed PMID: 25847999; PubMed Central PMCID: PMC4413288. 5: Remes C, Paun A, Zarafu I, Tudose M, Caproiu MT, Ionita G, Bleotu C, Matei L, Ionita P. Chemical and biological evaluation of some new antipyrine derivatives with particular properties. Bioorg Chem. 2012 Apr-Jun;41-42:6-12. doi: 10.1016/j.bioorg.2011.12.003. Epub 2012 Jan 2. PubMed PMID: 22257969. 6: Ikeda K, Iwasaki Y. Edaravone, a Free Radical Scavenger, Delayed Symptomatic and Pathological Progression of Motor Neuron Disease in the Wobbler Mouse. PLoS One. 2015 Oct 15;10(10):e0140316. doi: 10.1371/journal.pone.0140316. eCollection 2015. PubMed PMID: 26469273; PubMed Central PMCID: PMC4607459. 7: Zhu Y, Liu C, Sun Z. Early Combined Therapy with Pharmacologically Induced Hypothermia and Edaravone Exerts Neuroprotective Effects in a Rat Model of Intracerebral Hemorrhage. Cell Biochem Biophys. 2015 Nov;73(2):581-587. doi: 10.1007/s12013-015-0584-x. PubMed PMID: 27352357. 8: Deng L, Zhang L, Guo H, Jia L, Pan Y, Yin H, Qi F. VUV photon-induced ionization/dissociation of antipyrine and propyphenazone: mass spectrometric and theoretical insights. J Mass Spectrom. 2010 Jul;45(7):734-9. doi: 10.1002/jms.1763. PubMed PMID: 20623486. 9: Böttcher J, Bässmann H, Schüppel R. Quantitation and urinary pattern of 4,4'-dihydroxy-antipyrine, 4-hydroxy-antipyrine and 3-hydroxymethyl-antipyrine, as main metabolites of antipyrine in man and rat. J Pharm Pharmacol. 1982 Mar;34(3):168-75. PubMed PMID: 6121894. 10: Yang J, Cui X, Li J, Zhang C, Zhang J, Liu M. Edaravone for acute stroke: Meta-analyses of data from randomized controlled trials. Dev Neurorehabil. 2015;18(5):330-5. doi: 10.3109/17518423.2013.830153. Epub 2013 Oct 2. PubMed PMID: 24088023. 11: Nakajima N, Watanabe S, Kiyoi T, Tanaka A, Suemaru K, Araki H. Evaluation of edaravone against radiation-induced oral mucositis in mice. J Pharmacol Sci. 2015 Mar;127(3):339-43. doi: 10.1016/j.jphs.2015.02.001. Epub 2015 Feb 9. PubMed PMID: 25837932. 12: MacLean MA, Diez-Cecilia E, Lavery CB, Reed MA, Wang Y, Weaver DF, Stradiotto M. Diversification of edaravone via palladium-catalyzed hydrazine cross-coupling: Applications against protein misfolding and oligomerization of beta-amyloid. Bioorg Med Chem Lett. 2016 Jan 1;26(1):100-4. doi: 10.1016/j.bmcl.2015.11.022. Epub 2015 Nov 10. PubMed PMID: 26598460. 13: Sun Y, Yu C, Liu Z, Huang C, Hao Q, Xu L. Synthesis, structure, photo-responsive properties of 4-(2-fluorobenzylideneamino)antipyrine: a combined experimental and theoretical study. Spectrochim Acta A Mol Biomol Spectrosc. 2012 Nov;97:1013-22. doi: 10.1016/j.saa.2012.07.117. Epub 2012 Aug 4. PubMed PMID: 22925977. 14: Ji L, Liu Y, Zhang Y, Chang W, Gong J, Wei S, Li X, Qin L. The antioxidant edaravone prevents cardiac dysfunction by suppressing oxidative stress in type 1 diabetic rats and in high-glucose-induced injured H9c2 cardiomyoblasts. Can J Physiol Pharmacol. 2016 Sep;94(9):996-1006. doi: 10.1139/cjpp-2015-0587. Epub 2016 May 18. PubMed PMID: 27376621. 15: Watanabe A, Mayumi K, Nishimura K, Osaki H. In vivo use of the CYP inhibitor 1-aminobenzotriazole to increase long-term exposure in mice. Biopharm Drug Dispos. 2016 Sep;37(6):373-8. doi: 10.1002/bdd.2020. Epub 2016 Aug 24. PubMed PMID: 27379984. 16: Hu H, Sun Xo, Tian F, Zhang H, Liu Q, Tan W. Neuroprotective Effects of Isosteviol Sodium Injection on Acute Focal Cerebral Ischemia in Rats. Oxid Med Cell Longev. 2016;2016:1379162. doi: 10.1155/2016/1379162. Epub 2016 Mar 7. PubMed PMID: 27047634; PubMed Central PMCID: PMC4800105. 17: Ren Y, Wei B, Song X, An N, Zhou Y, Jin X, Zhang Y. Edaravone's free radical scavenging mechanisms of neuroprotection against cerebral ischemia: review of the literature. Int J Neurosci. 2015;125(8):555-65. doi: 10.3109/00207454.2014.959121. Epub 2014 Sep 24. Review. PubMed PMID: 25171224. 18: Carbone F, Teixeira PC, Braunersreuther V, Mach F, Vuilleumier N, Montecucco F. Pathophysiology and Treatments of Oxidative Injury in Ischemic Stroke: Focus on the Phagocytic NADPH Oxidase 2. Antioxid Redox Signal. 2015 Aug 10;23(5):460-89. doi: 10.1089/ars.2013.5778. Epub 2014 Apr 22. Review. PubMed PMID: 24635113; PubMed Central PMCID: PMC4545676. 19: Parikh A, Kathawala K, Tan CC, Garg S, Zhou XF. Development of a novel oral delivery system of edaravone for enhancing bioavailability. Int J Pharm. 2016 Dec 30;515(1-2):490-500. doi: 10.1016/j.ijpharm.2016.10.052. Epub 2016 Oct 24. PubMed PMID: 27789367. 20: Lu HC, Chang WJ, Kuan YH, Huang AC, Shyu BC. A [14C]iodoantipyrine study of inter-regional correlations of neural substrates following central post-stroke pain in rats. Mol Pain. 2015 Mar 8;11:9. doi: 10.1186/s12990-015-0006-5. PubMed PMID: 25889278; PubMed Central PMCID: PMC4358859.

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